Ethylene Glycol → 2-(1,3-Dioxolan-2-yl)-3-nitropyridine

HRID 473403

反応式

HRID 473403 の反応式
[N+:1]([C:4]1[C:5]([CH:10]=[O:11])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].CC1C=CC(S(O)(=O)=O)=CC=1.[CH2:23](O)[CH2:24][OH:25].O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[O:11]1[CH2:23][CH2:24][O:25][CH:10]1[C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=[CH:7][N:6]=1

参加物

7

反応物 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 3293613-Nitropicolinaldehyde

生成物 1

HCID 3293622-(1,3-Dioxolan-2-yl)-3-nitropyridine

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

3-Nitro-2-pyridinecarbaldehyde (22 g, 144.74 mmol) was dissolved in toluene (500 mL). To the mixture was added catalytic amount of p-TSA (2 g) and ethylene glycol (40 mL) and the reaction flask equipped with Dean-Stark assembly was refluxed for 12 h at 120° C. After the reaction was complete, the reaction mixture was treated with water and ethyl acetate. The organic layer was separated and the aqueous layer was back extracted with ethyl acetate. The organic layers were combined and dried over anhydrous Na2SO4 and concentrated under reduced pressure to give a thick oily mass. The oily mass was then purified by silica gel column chromatography using 20% of ethyl acetate and hexane as eluent to give 2-(1,3-dioxolan-2-yl)-3-nitropyridine: 1H-NMR (CDCl3) δ: 4.2 (d, 5H), 6.5 (s, 1H), 7.5 (m, 1H), 8.3 (d, 1H), 8.9 (brs, 1H).

後処理

  1. customthe reaction flask equipped with Dean-Stark
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was back extracted with ethyl acetate
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto give a thick oily mass
  7. customThe oily mass was then purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-0e6942b0b24047c6b74d017462bca360
出典データセット
uspto-grants-2014_01
特許番号
US08633313B2

関連ノート

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